West Stringfellow

I build and lead teams that create platforms years before they’re obvious.

Two-time Chief Product & Technology Officer. Two-time founder & CEO, one acquired by Target. An operating executive since 2008, with 5 technology patents.

West Stringfellow
Innovated at
Resulted in
98%
fraud losses cut with machine learning at Amazon
12x
market expansion from PayPal’s first omnichannel wallet
$120B+
in payments on the platform my organization ran
1,000+
people led across nine global locations
AI Leadership

Twenty years of AI in production.

Automating and accelerating production systems with hundreds of millions of dollars in revenue and risk attached, two decades ago.

2005
Amazon Amazon was losing real money to marketplace fraud in Europe. Our merchant-risk team built machine-learning models that cut those losses 98%, an early lesson in what AI does when it’s pointed at a P&L problem. The same year, I proposed Amazon’s first paid web service, the Historical Pricing API: data sold as a product, five months before S3.
2008
Visa Verified by Visa asked shoppers to remember yet another password at checkout. My team rebuilt it around machine-learning risk scoring that verified people silently in the background, with no password unless the model saw something suspicious. Usage grew 130% year over year.
2013
Rosetta Stone Rosetta Stone taught language by listening to customers speak and responding. The speech-recognition and natural-language systems behind that experience were run by the 160-person organization I led: AI inside the core revenue product, serving millions of paying customers.
2016
Every (acquired by Target)

At Every, our 28-person team built a patented social-commerce platform that used machine learning to match influencers with products and consumers, three years before Meta launched shopping. Target acquired the company months after launch.

2025
Blackhawk Network Blackhawk had no enterprise AI platform, so I built the case for one: 25 stakeholder meetings, a 150-person pilot that proved immediate ROI, then a rollout of Claude to 1,000+ employees. The clearest evidence it works: my five-person product team, operating AI-natively, delivers double the output of peer teams of sixty-plus.
Now
Founder & CEO, HowDo Started in 2017 with a team of 18 and self funded, we built an AI mentor for entrepreneurs: ask it a business question in plain English, get an answer drawn from 50,000+ hand-curated data points. We were working on the problems ChatGPT made famous, five years before ChatGPT. Alongside it, we built the world’s largest open-source innovation course. It reached 400,000+ learners and led to my selection as an Edmund Hillary Fellow. Today: building the next generation business platform, again. Learn more at HowDo.com
Track Record

Building teams that (re)build businesses.

The teams I lead build and transform products, platforms, and P&Ls.

Amazon

Product Manager, twice promoted · 2004–2007 · Seattle · Bangalore · London

I joined Amazon as a product manager and left three years and two promotions later. With small teams and large mandates, we designed and launched Amazon’s first digital video platform and operations, the foundation of what is now Prime Video. I proposed and championed Amazon’s first paid web service, the Historical Pricing API, launched October 2005, five months before S3. I proposed and built Amazon’s first fraud office in Bangalore, which grew into its largest office of fraud analysts. Our European merchant-risk team used machine learning to cut fraud losses 98%.

Payments: Visa & PayPal

VP of Innovation & eCommerce, Visa 2007–2009 · Senior Director of Product & Platform, PayPal 2010–2012

At Visa, my 22-person team built the company’s first direct-to-consumer payment product, work that earned two patents, and rebuilt Verified by Visa around machine-learning passive authentication, growing usage 130% year over year.

At PayPal, I led a 1,000-person product, engineering, and design organization across nine global locations. Together we proposed and built the first omnichannel wallet and point-of-sale payments platform, launching with Home Depot, Abercrombie & Fitch, and Ingenico: a 12x expansion of PayPal’s addressable market, recognized with PYMNTS’ “Most Innovative” award. Running the product and technology organizations responsible for 110M+ users and $120B+ in payments, cutting $25M in annual costs, and rebuilding PayPal Australia’s compliance operations which retained 3M+ consumers.

Rosetta Stone & BigCommerce

Chief Product & Technology Officer at both · 2012–2014 · San Francisco · Sydney

At Rosetta Stone, with a rebuilt 160-person team and a $45M budget, we pivoted the company from boxed software to digital, cutting cost of goods 80% and growing active customers 1,000%. We took the mobile app from 1 star to 4.5 stars (1M+ new downloads, 8x conversion) and shipped six new products in a year at a company that hadn’t launched one in six, including Advanced English for Business (NPS 50+, $1M+ revenue in its first quarter) and a kids title that reached #2 on iTunes’ free kids chart and won iKids’ Best Learning App. We also integrated three acquisitions.

At BigCommerce, I rebuilt a 115-person product and technology organization across Austin, San Francisco, and Sydney, standing up the San Francisco office with 60+ hires in four months. We repositioned the SaaS strategy toward high-value merchants, helping secure a $50M Series D, and took platform availability from 94% to 99.9% across 130,000 storefronts.

Every → Target

Founder & CEO, Every · VP of Innovation & Entrepreneur in Residence, Target · 2014–2017

I founded Every in 2014: social commerce, three years before Meta launched shopping. We raised $27M, and I recruited a 28-person team that included executives from Netflix, PayPal, and Uber. We built a patented AI-matching commerce platform and acquired two startups to accelerate it. Months after launch, Target acquired the company.

Inside Target, I served as their first Entrepreneur in Residence, then VP of Innovation: my team cut $100M+ in low-performing projects, reallocated $30M+ to growth initiatives, and ran a Techstars accelerator inside Target: 530 applications from 45 countries in year one, twice the Techstars average, supported by 130 Target mentors. That work became Target Accelerators, today a permanent Target business function. Minnesota’s business community named me to its “Real Power 50.”

Capabilities

My favorite things about business.

Zero to one

Amazon’s first digital video platform. Visa’s first direct-to-consumer payment product. PayPal’s first omnichannel wallet. Target’s first startup accelerator. When something has to exist and doesn’t yet, that is my favorite assignment.

Teams that create industries

New industries are built by great teams. I have had the opportunity to build and rebuild product and technology organizations at inflection points and scale them: 115 people at BigCommerce, 160 at Rosetta Stone, over 1,000 at PayPal across nine global locations, and now small, talented teams and AI.

AI & technology strategy

Two decades of AI in production: fraud, authentication, natural language processing (NLP), natural language generation (NLG), and current enterprise-scale deployment. Translated into strategy: where AI creates enterprise value, what it costs, and how to govern its risk.

M&A on both sides of the table

Founded and sold a company to Target; acquired two startups at Every; led diligence and integration of three acquisitions at Rosetta Stone.

Regulated markets

Rebuilt PayPal Australia’s compliance operations under regulatory pressure, retaining 3M+ consumers.

Global operations

Operated businesses and teams across the US, UK, Europe, Australia, Asia, and India.

Recognition
2025

Product Leader, Products That Count

2020

Edmund Hillary Fellowship. Selected as a Fellow for global innovation impact.

2016

(Real) Power 50, Minnesota Business Magazine. Named while VP of Innovation at Target.

2014

Best Learning App, iKids Awards. A unanimous jury decision, for Rosetta Stone’s kids series.

2013

“Most Innovative,” Gold, PYMNTS Innovator Awards. For PayPal’s omnichannel payments platform.

2010

Google Zeitgeist Award. For SEO growth at GraysOnline.